I would follow the advice above and protect your assets and I wouldn't let a boyfriends fears deter you.

Every state has some built-in bankruptcy protections for some of your assets so that you're not out on the street.

Renters here are savvy and it's common knowledge to hold out at the LL's expense while fully protected.

How do I make this a win-win and protect myself at the same time.I'm thinking using hard money to buy outright, than refi'ing to lower the mortgage and putting a tenant in it unless I can sell it but buy and hold is more my play...I'm open to ALL input and expertise...

Unfortunately I have seen this before, older people transfer assets to protect them from paying fees for extended care then the kids get into trouble and the entire thing backfires on them.

I have an investor that interested in backing us on our next venture and we are collectively trying to figure out what type of documents need to be drawn up to protect both us and the investor. 

The reason I say this is because the purpose of an entity is for protection and tax purposes.

I am starting to consider moving these properties to an LLC for asset protection, a step that I knew was necessary later down the road, but which I punted on while getting started.I planned to establish an LLC in the state of West Virginia and put the properties in it.

Any good tips or ways to structure insurance so you get good protection but it doesn't kill cash flow?

On the IRS website:from https://www.irs.gov/businesses/small-businesses-self-employed/forms-and-associated-taxes-for-independent-contractorsChanges for 2016A new federal law, the Protecting Americans from Tax Hikes (PATH) Act, enacted in December 2015, moves up some 1099-MISC filing deadlines to January 31.